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Travel Advisor: Allison Yaeger
(443) 340-7755
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Pleasant Holidays offers curated vacation experiences to some of the world’s most sought-after destinations, including Hawaii, Mexico, the Caribbean, and Europe. Whether you're dreaming of a tropical beach escape, a cultural European adventure, or a family getaway, Pleasant Holidays has the perfect trip tailored to your needs.

Choose from a wide variety of options to match your style and budget. Your next unforgettable adventure with Pleasant Holidays is waiting.

Start planning today and create memories that will last a lifetime!

  • Beaches Turks & Caicos Resort Villages and Spa

    Turks and Caicos Islands
    All-Inclusive Family-Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • $300 Off Vacation Package
  • Hammock Cove Antigua

    Antigua
    All-Inclusive Adults Only
    Call for Special Pricing (443) 340-7755

    Offers & More

      • $300 Off Vacation Package
  • Moon Palace Jamaica

    Ocho Rios, Jamaica
    All-Inclusive Family-Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • $300 Off Vacation Package
      • Receive up to $250 Resort Credit
      • Kids 17 & Younger Stay, Play and Eat FREE
  • Riu Palace Aquarelle

    Montego Bay, Jamaica
    All-Inclusive Family-Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • $300 Off Vacation Package
      • Receive Up to $762 in Resort Coupons
  • ‘Alohilani Resort Waikiki Beach

    Honolulu, Hawaii
    Family Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • Across from Waikiki Beach
      • Near the Honolulu Zoo, Waikiki Aquarium and Waikiki Shell Amphitheater
      • Historical Iolani Palace and Polynesian Cultural Center Nearby
  • Aston Kaanapali Shores

    Lahaina, Hawaii (Maui)
    Family Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • Beachfront Location
      • Hula Lessons, Pickleball Court, Lei Making
      • Golf Nearby
  • The Twin Fin

    Honolulu, Hawaii
    Family Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • Across from Waikiki Beach
      • Near Kapiolani Park and the Honolulu Zoo
      • Putting Green, Tennis Court, Snorkeling
  • Waikoloa Beach Marriott Resort & Spa

    Waikoloa, Hawaii (Big Island)
    Family Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • Located on the Kohala Coast with a Sandy and Swimmable Beach
      • Two Championship Golf Courses
      • Live Entertainment, Sailing, Snorkeling, Surfing
  • Wailea Beach Resort - Marriott, Maui

    Wailea, Maui
    Family-Friendly
    Call for Special Pricing (443) 340-7755

    Offers & More

      • Beachfront location
      • Near Three Championship Golf Courses
      • Sailing, Snorkeling, Hiking